Methanol → 4-(2,4-dihydroxymethylphenyl)-5-methyl-2-[N-(alpha-cycloproplybenzyl)-N-propylamino]thiazole

HRID 399638Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[C:8]([C:10](O)=[O:11])[CH:7]=[CH:6][C:5]=1[C:13]1[N:14]=[C:15]([N:19]([CH:23]([CH:30]2[CH2:32][CH2:31]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:21][CH3:22])[S:16][C:17]=1[CH3:18])(O)=[O:2].B.C(=O)([O-])[O-].[K+].[K+].CO>O1CCCC1.O>[OH:2][CH2:1][C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:5]=1[C:13]1[N:14]=[C:15]([N:19]([CH:23]([CH:30]2[CH2:31][CH2:32]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:21][CH3:22])[S:16][C:17]=1[CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

1 g of the compound obtained in Step A is dissolved in 20 ml of anhydrous tetrahydrofuran, followed, at -7° C., by addition of 5 ml of 1M borane solution in tetrahydrofuran, and the mixture is stirred overnight. 0.5 g of potassium carbonate and 10 ml of a mixture of methanol and water (1:1 v/v) are then added. The mixture is maintained at 60° C. for 2 hours and then cooled and evaporated under vacuum. The residue is taken up in water and extracted with ethyl ether, and the organic phase is washed with water, then with saturated aqueous sodium chloride and dried over anhydrous sodium sulphate. It is evaporated to dryness and the residue is taken up in pentane. The expected product is thus obtained.

Workup

temperaturecooled
customevaporated under vacuum
extractionextracted with ethyl ether
washthe organic phase is washed with water
dry with materialwith saturated aqueous sodium chloride and dried over anhydrous sodium sulphate
customIt is evaporated to dryness

Sources & evidence

ORD record: ord-ea83c9ff24a245f2b6a63b23862af4bd
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05821255

Reaction notes

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